Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 20, Problem 48P
Interpretation Introduction
Interpretation:
The reasonable structure for compound
Concept introduction:
The replacement or substitution of one functional group with another different functional group in any
In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom.
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On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) yielded a mixture of two alkenes B and C, each having the molecular formula C7H14. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.
Compound A was oxidized with periodic acid to give B, which after acid hydrolysis gave C. Bromine oxidation of C gave D. Suggest structural formulas, including stereochemistry, for compounds B, C, and D.
Compound A(C10H12O)gives off oxygen on treatment with sodium metal and also decolorizes Br2 in CCl4 to give organic compound B. Compound A on treatment with I2 in NaOH gives iodoform and salt C which after acidification gives a white solid D(C7H6O2). Using knowledge of organic chemistry identify structures A,B,C and D
Chapter 20 Solutions
Organic Chemistry - Standalone book
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.3 - Prob. 3PCh. 20.4 - Prob. 4PCh. 20.5 - Prob. 5PCh. 20.8 - Prob. 6PCh. 20.8 - Prob. 7PCh. 20.8 - Prob. 8PCh. 20.9 - Prob. 9PCh. 20.9 - Prob. 10P
Ch. 20.9 - Prob. 11PCh. 20.9 - Prob. 12PCh. 20.10 - Prob. 13PCh. 20.10 - Prob. 14PCh. 20.11 - Prob. 15PCh. 20.11 - Prob. 16PCh. 20.11 - Prob. 17PCh. 20.12 - Prob. 18PCh. 20.12 - Prob. 19PCh. 20.12 - Prob. 20PCh. 20.12 - Prob. 21PCh. 20.13 - Prob. 22PCh. 20.13 - Prob. 23PCh. 20.14 - Prob. 24PCh. 20.15 - Prob. 25PCh. 20.16 - Prob. 26PCh. 20.17 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Write a structural formula for the principal...Ch. 20 - Prob. 32PCh. 20 - Prob. 33PCh. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - The preparation of the sex pheromone of the...Ch. 20 - Prob. 44PCh. 20 - Suggest a reasonable explanation for each of the...Ch. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - A compound has a molecular formula of C8H14O4, and...Ch. 20 - Prob. 51PCh. 20 - Prob. 52DSPCh. 20 - Prob. 53DSPCh. 20 - Prob. 54DSPCh. 20 - Prob. 55DSPCh. 20 - Prob. 56DSPCh. 20 - Thioesters Thioesters have the general formula ....Ch. 20 - Prob. 58DSP
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- A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired conguration.a. Label this stereogenic center as R or S.b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.c. Suggest a reagent to convert A to the single stereoisomer X.arrow_forwardWolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.arrow_forwardA difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. c. Suggest a reagent to convert A to the single stereoisomer X.arrow_forward
- Compound A is an alcohol that undergoes oxidation to produce compound B.Compound B is a ketone that gives positive triiodomethane reaction. Compound B isthen reacted with phenyl magnesium bromide, C6H5MgBr in the presence of aqueousacid to form compound C. Compound C has the molecular formula of C9H12O. Deducethe structure for compound A, B and C. PLEASE PROVIDE CLEAR DRAWINGS AND EXPLANATIONSarrow_forwardOn being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a mixture of two alkenes B and C, each of which had the molecular formula C7H14. Catalytic hydrogenation of major isomer B or minor isomer C gave only 3-ethylpentane. Suggest structures and mechanisms for compounds A, B, and C consistent with these observations.arrow_forwardPyrethrin II and pyrethrosin are two natural products isolated from plants of the chrysanthemum family. Pyrethrin II is a natural insecticide and is marketed as such. Q, Show that the bicyclic ring system of pyrethrosin is composed of three isoprene units.arrow_forward
- Deduce the structure of compound C.arrow_forwardCompound A, C3H7Br, does not react with cold dilute potassium permanganate solution. Upon treatment with potassium hydroxide in ethanol, A gives only product B, C3H6. Unlike A, B decolourises potassium permanganate solution. Ozonolysis of Bgives C, C2H4O, and D, CH2O. Suggest the structural formulae of A, B, C and D.Write the equations for all the reactions involved.arrow_forwardA compound A, C7H12, was found to be optically active. On catalytic reduction over platinum catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, C7H16. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid. The other fragment, compound C, was an optically active carboxylic acid, C5H10O2. Write the reactions and draw structures for A, B and C.arrow_forward
- Compound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…arrow_forwardIdentify the hemiacetal function in lactose and show mechanistically how the stereochemistry at that carbon can easily invert, especially in the presence of acids and bases.arrow_forwardCompound P (C2H4) which is an alkene undergoes reaction with HCl to produce compound Q (C2H5Cl). Reaction of compound Q with benzene in the presence of AlCl3 as catalyst produces compound R. Then, nitration of compound R in the presence ofnH2SO4 produces two compounds, S and T. But when compound R is reacted with a hot acidified solution of alkaline KMnO4 gives compound U. Deduce the structure of compounds P to U.arrow_forward
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